Stable depilatory compositions



United States Patent ice 3,154,470 STABLE DEPILATORY COMPOSITIONS Ernest Braun, Forest Hills, N.Y., and John E. Logun,

North Caldwell, N.J., assignors to Chemway Corporation, Wayne, NJ, a corporation of Delaware No Drawing. Filed Dec. 27, 1962, Ser. No. 247,550 3 Claims. (Cl. 16789) This invention relates to a depilatory composition. More particularly, this invention relates to a stable depilatory composition wherein the essential active depilating agent is a substituted thiol in which the hydrogen atom in hydrogen sulfide is substituted by various organic residues and wherein the active depilating agent is intimately dispersed in a particular emulsified emollient base which provides a protective mantle to prevent skin irritation by the active depilating agent.

Depilatory compositions containing substituted thiols, particularly thioglycollates, are well known in the art and are commercially available generally as pastes or creams or as powders to be admixed with water to form a paste just prior to use. Such depilatory compositions necessarily have a pH of at least about and require removal within a relatively short time to prevent skin irritation. Although such depilatory compositions have had limited acceptance, there is a need in the art for an effective, fast acting, stable depilatory composition which can be left in contact with the skin for prolonged periods of time without causing skin irritation or other side elfects. This need is particularly acute where hospital preoperative depilating procedures are involved, especial ly where the area to be depilated is already irritated or lacerated.

The depilatory compositions of this invention are unique in that they can be left in contact with the skin for prolonged periods of time without causing skin irritation or other side effects. They are effective in that complete depilation is accomplished in time periods of the order of ten minutes. Moreover, it has been found that after prolonged periods of application to the skin of upwards of an hour or more, the depilatory compositions of this invention do not dry out, can be readily removed, and do not form offensive sulphidic odors. Also, the depilatory compositions of this invention are in a form that, when packaged in tubes, are indefinitely stable.

The depilatory compositions of this invention consist essentially of (a) an emollient base comprising from about 30 to 70 percent by weight of at least one monoamide of a C to C monocarboxylic acid and an alkanolamine selected from the class consisting of primary and secondary lower alkanolamines, from about to about 30 percent by weight of at least one Kritchevsky condensate of a C to C monocarboxylic acid and an alkanolamine selected from the class consisting of primary and secondary lower alkanolamines, the Kritchevsky condensate having an acid number from about 40 to 60 and an alkali number from about 70 to 200, and from about 15 to 50 percent by weight of a nonionic oil-in-water emulsifier selected from the class consisting of polyol esters of fatty acids and polyalkenoxy type surface active agents, the emollient base having a melting point between about 65 and 100 C., (b) sufiicient water emulsified with the emollient base to provide a cream-like consistency to the emollient base, said emulsified components (a) and (b) having intimately dispersed therein, (0) a solid basic material selected from the class consisting of guanadine and alkali and alkaline earth metal hydroxides, carbonates, silicates, and tribasic phosphates in an amount sufiicient to provide a pH in 3,11%,43'0 Patented Got. 2?, 1964 the resulting admixture of 10.5 to 12.5, and (d) as the essential active depilating agent, an effective depilating amount of a substituted thiol in which the hydrogen atom in hydrogen sulfide is substituted by an organic residue containing two to four carbon atoms and at least one of a group selected from the class consisting of hydroxyl, ketone, aldehyde, ether, amine, sulfonic acid, carboxylic acid and carboxylic acid salt groups.

The emollient base serves to provide a protective mantle to prevent skin irritation. It is prepared from three essential components, a monoamide of an. alkanolamine and a C to C monocarboxylic fatty acid, a Kritchevsky condensate of a C to C monocarboxylic acid and an alkanolamine, and a non-ionic oil-in-water emulsifier which can be a polyol ester of a fatty acid or a polyalkenoxy type surface active agent.

The first component, the monoamide of an alkanolamine and a C to C monocarboxylic fatty acid and the second component, the Kritchevsky condensate of an alkanolamine and a C to C monocarboxylic acid, are well known to the art and are articles of commerce. The monoamides are prepared by heating approximately equal molar proportions of the fatty acid and the alkanolamine to a temperature in the range of about to 180 C. and distilling off the water formed in the condensation. They are not always obtained in highly pure form since a certain proportion of the fatty beta-aminoethyl ester is usually formed together with the amide, although a method of producing the amide relatively free of aminoester has been described in British Patent No. 693,086. These monoamides generally have an acid number from about 0 to 5 and an alkali number of from about 5 to 50. The Kritchevsky or Ninol condensates, on the other hand are prepared by heating one mole of the fatty acid and two moles of the alkanolamine to a temperature in the range of about to C. and distilling off the water formed in the condensation until the amount of water has almost reached the theoretical quantity required for monoamide formation. When the free fatty acid content has fallen to the range of about 5% or less, the reaction is stopped. The product is a high viscosity liquid soluble in water having a pH of about 9. The method of preparation is described in US. Patents 2,089,212; 2,094,608 and 2,094,609 to Kritchevsky and the reaction mechanism is described at pages 212-213 of Surface Active Agents, Schwartz and Perry, Interscience Publishers, Inc. (1949). Kritchevsky condensates having an acid number from about 40 to 60 and an alkali number from about 70 to 200 are used to form the depilatory compositions of this invention.

The C to C monocarboxylic acids used to form the monoamides and the Kritchevsky condensates are the usual saturated and unsaturated fatty acids of commerce and include caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, palmitoleic acid, linoleic acid, linolenic acid and natural and synthetic admixtures of these acids, such as coconut oil fatty acids, soybean oil fatty acids, and the like. The alkanolamines used to form the monoamides and the Kritchevsky condensates are the lower alkanolamines having a primary or secondary amino group such as monoethanolamine, diethanolamine, ethylethanolarnine, monopropanolamine, dipropanolamine, ethylpropanolarnine, and the like. Similar amines such as trimethylaminomethane and diglycerylamine can also be used.

The third component of the emollient base is a nonionic type oil-in-water emulsifier. The non-ionic polyol esters of fatty acids include those formed from the C to C higher fatty acids mentioned above and polyols such as sorbitol, mannitol, pentaerythritol, the polypentaerythritols, glycerol, the polyglycerols, and-the glucosides. The non-ionic polyalkenoxy type oil-in-water emulsifiers include those conventionally employed in cosmetic and pharmaceutical preparations. Thus there can be used the conventional non-ionic polyethenoxy type surface active agents and these include the oxyethylated polyoxypropylene glycols described in U.S. Patent 2,674,619 to Lundsted and sold commercially as Pluronics, the oxyalkylated partial esters of polyhydric alcohols and fatty acids described in US. Patent 2,380,166 and sold commercially as Tweens, the benzyl ethers of alkylphenoxy polyethoxyethanols described in U.S. Patent 2,856,434 to Niederhauser and sold commercially as Triton CF10, the polyoxyalkylene surfactants described in US. Patents 2,677,700, 3,036,118 and 3,036,130 to Jackson et al., the mixed higher polyoxyalkylene ethers of hexitols described in U.S. Patent 2,673,882 to Grifiin, alkylphenoxy polyoxyethylene ethanols produced by the reaction of an alkylphenol with ethylene oxide and sold commercially as Igepals, the oxyalkylated glycerols, produced by reaction with glycerol of a mixture of ethylene and propylene oxides, marketed by Dow Chemical Co., and the fatty alcohol ethers such as the cetyl, stearyl, lauryl or oleyl ethers of ethylene oxide polymers.

One of the primary functions of the monoamide in the emollient base is to provide body to the final depilatory composition. The proportion of monoamide in the emollient base can, therefore, vary widely between about 30% and 70% depending upon the consistency desired in the final depilatory composition, i.e., a proportion within the lower portion of the range for a relatively free flowing cream and a proportion within the upper portion of the range for a full-bodied cream or paste. A small proportion of the monoamide can be replaced by filler materials such as methyl cellulose or gum tragacanth.

One of the primary functions of the Kritchevsky condensate is to thicken the emulsion formed from the water, monoamide and non-ionic polyalkenoxy type oil-in-water emulsifier. Another important function is to suspend the undissolved portions of the solid basic material and the substituted thiol. For these reasons the proportion of Kritchevsky condensate in the emollient base is within the range of about to 30% by weight.

The function of the non-ionic emulsifier is to emulsify the slightly soluble or dispersible monoamide in the water. Thus the proportions of non-ionic oil-in-water emulsifier can vary widely from about 15 to 50% by weight of the emollient base depending upon the relative proportions of the other components.

The emollient base must have a melting point of about 65 to 100 C. so that the particular components should be selected and their proportions chosen Within the described ranges as to provide a base having a melting point within this range. Ordinarily the emollient base will constitute between about 10% to by weight of the final depilatory composition, preferably about 16 to 22% by weight.

Sufiicient water is emulsified with the emollient base to provide a cream-like consistency to the emollient base. Ordinarily the amount of Water so emulsified will constitute between about 50% to 70% by weight of the final depilatory composition.

The active depilating agent of the compositions of this invention is a substituted thiol in which the hydrogen atom in hydrogen sulfide is substituted by an organic residue containing two to four carbon atoms and at least one of a group selected from the class consisting of hydroxyl, ketone, aldehyde, ether, amine, sulfonic acid, carboxylic acid and carboxylic acid salt groups. Such materials are well known and are described in US. Patent 2,352,524 issued June 27, 1944, to Ralph L. Evans et al. and British Patent 521,240 (1940) to Ralph L. Evans et al. As explained in those patents, the thiol group normally has a pronounced disagreeable odor unless the organic group attached to the thiol group has one or more substituent groups such as hydroxyl, ketone, aldehyde, ether, amine, sulfonic acid, carboxylic acid or carboxylic acid salt groups. The most effective and least odoriferous are the guanadine, ethylene diamine, alkali and alkaline earth metal salts of thioglycollic acid and thiolactic acid, including specifically the guanadine, ethylene diamine monoand di-, sodium, potassium and calcium thioglycollates and thiolacetates. The preferred active agent is calcium thioglycollate. The final depilatory composition will generally contain about 3 to 15 percent by weight of the substituted thiol.

The activating agent for the thioglycollate is a solid basic material which can be any of guanadine or the alkali and alkaline earth metal hydroxides, carbonates silicates, and tribasic phosphates, preferably iron free since iron forms discoloration in the presence of a substituted thiol. The solid basic substance must be present in an amount sufficient to provide a pH of 10.5 to 12.5, preferably 11 to 12, in the final depilatory composition and ordinarily will constitute between about 4% to 15% by weight of the final depilatory composition. A lower pH requires more time for eifective depilation and a higher pH tends to produce irritation.

In addition to the above essential components, the depilatory compositions of this invention can contain minor amounts, i.e., up to about 5% by weight of the final depilatory compositions, of other materials conventionally employed in formulating cosmetics and depilating agents. Thus they can contain coloring matter, such as vegetable and synthetic dyes, perfumes, including animal perfumes such as musk, civet, ambergris and castor, as well as vegetable perfumes such as sage, thyme, mint, cinnamon, cassia, cedar, sandal wood, rose, violet, anise, caraway, orris, orange, camphor and myrrh and mixtures thereof. They can contain bacteriostats, such as bithionol, hexetidine, hexachlorophene and the like. They can contain sodium sulfite as an antioxidant, zinc oxide to reduce odor, urea to thicken the hair, and solvents such as propylene glycol and glycerine to provide smoothness and homogeneity to the cream.

In formulating the depilatory compositions of this invention, the components of the emollient base are first admixed and heated to above the melting point of the admixture to provide the emollient base in liquid phase. The emollient base in liquid phase is then slowly added and intimately admixed with about two-thirds of the water, heated to about the same temperature, until a uniform emulsion has formed and then cooled to room temperature while mixing. In a separate vessel, a solutionsuspension of the solid basic material and the substituted thiol is formed in the remainder of the water at about room temperature. The solution-suspension of basic material is then slowly admixed with the emulsified emollient base. The finished cream should be thoroughly covered to prevent oxidation or immediately packaged, for example, in tubes.

Depilatory compositions of this invention are illustrated by the following examples. In the examples, commercial monoamides and Kritchevsky condensates were employed. The monoamide in each instance was a mixture of Monoamide A, the monoethanolamide of lauric acid and Monoamide B, the monoethanolamide of stearic acid. Monoamide A is a light yellow solid in flake form with a melting point of 8993 C. and an acid value of 10-14. It is dispersible in water at elevated temperatures and a 3% dispersion in water at 25 C. has a pH of 8.0 to 9.5. Monoamide B is a light tan solid in flake form with a melting point of 69-73 C. and an acid value of 1014. It is dispersible in water at elevated temperatures and a 3 dispersion in water at 25 C. has a pH of 89.5. The Kritchevsky condensate employed was a condensate of diethanolamine and a mixture of 60 percent coconut oil fatty acids and 40% oleic acid. It was an amber liquid, having a pH of 9.5 in aqueous solution, an acid number of 45-50, and an alkali number of 115-125. The non-ionic oil-in-water emulsifiers employed were Emulsifier A, sorbitan sesquioleate, Emulsifier B, sorbitan trioleate and Emulsifier C, an oxyethylated sorbitan monooleate (Tween 80).

EXAMPLE 1 Into a first stainless steel container were placed 3.250 kilograms of Monoamide A, 3.000 kilograms of Monoamide B, 2.250 kilograms of the Kritchevsky condensate, 1.750 kilograms of Emulsifier B and 0.500 gram of bithionol. These materials were heated to a temperature of 90 C. to form the liquid phase emollient base.

Into a second stainless steel container were placed 7.500 kilograms of distilled Water and dissolved therein were 0.004 kilogram of sodium hydroxide pellets, 1.500 kilograms of sodium sulfite crystals, 0.0005 kilogram of D & C #19 (tetraethylrhodamine) and 0.00075 kilogram of PD & C Red #3. These materials were heated to a temperature of 92 C. and the liquid phase emollient base at 90 C. in the first container was slowly added with mixing while maintaining the temperature-between 75 and 80 C. After about 30 minutes a uniform emulsion had developed and mixing was continued until the emulsion had cooled to room temperature.

Into a third stainless steel container were placed 7.500 kilograms of distilled water and slowly added thereto 4.200 kilograms of calcium thioglycollate, 1.000 kilogram of calcium hydroxide (USP) and 2.000 kilograms of milled strontium hydroxide. A portion of the solid materials dissolved and the resulting suspension was passed through an Eppenbach colloid mill, Model 2L, using a number opening. The milled suspension was then added to and admixed with the emulsion in the second container for ten minutes, 0.250 kilogram of perfume were added, and the resulting admixture was passed through the Eppenbach mill using a number 40 opening. The finished depilatory cream was then packaged in metal tubes.

The finished depilatory cream was tested for depilating action by smearing it on a male human lower leg having considerable hair. After ten minutes a portion of the cream was removed by wiping with a paper tissue leaving a skin area devoid of hair and stubble. After an additional twenty minutes the remainder of the cream was removed with another paper tissue. The complete skin area was devoid of hair and stubble, had a fragrant odor and the skin was free from any signs of irritation.

EXAMPLES 2-7 Additional depilatory compositions were prepared similarly as in Example 1. The components and amounts employed are shown in the following Table I. The amounts are in grams except in the cases of sodium hydroxide and thioglycollic acid wherein the amounts are in cubic centimeters.

Table I Example Component MonoamideA 4. 40 5.0 4.0 3.75 12.0 11.0 Monoamide B 1.00 2. 0 1. 0 1. 4. 0 3.0 Emulsifier A 3. 75 Emulsifier B 4. 5.0 5.0 4. 0 4. 0 Emulsifier C 1.60 1.5 1.5 1.0 1.0 0.5 Kritchevsky condensate 3. 0 3. 0 3. 0 3. 0 5. 0 3. 0 Triethanolamine 2. 0 Propylene Glycol 5.0 5.0 5.0 3.0 3.0 3.0 3.0 3.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 60. 0 57. 5 59. 5 64. 25 54. 0 56.5 0075 005 005 008 005 005 5.5 5.5 5.5 5.5 5.5 5.5 Sr(0H) 4.0 4.0 4.0 4.0 4.0 4.0 Thioglycollic Acid, 70%. 4. 5 4. 5 4.5 4.5 4.5 4. 5 Perfume 1. 0 1. 0 1. 0 1.0 1. 0 1. 0 Bithionol 1. 0 1. 0 1. 0 1. 0 1. 0 Methyl Cellulose, 4,000 cps. 2. 0

We claim:

1. A stable depilatory composition consisting essentially of (a) an emollient base comprising from about 30 to 70 percent by weight of at least one monoamide of a C to C monocarboxylic acid and an alkanolamine selected from the class consisting of lower alkanolamines having primary and secondary amino groups and having only lower alkyl and lower hydroxyalkyl substituents, from about 15 to about 30 percent by weight of at least one Kritchevsky condensate of a C to C monocarboxylic acid and an alkanolamine selected from the class consisting of lower alkanolamines having primary and secondary amino groups and having only lower alkyl and lower hydroxyalkyl substituents, the Kritchevsky condensate having an acid number from about 40 to 60 and an alkali number from about 70 to 200, and from about 15 to 50 percent by weight of a nonionic oil-in-water emulsifier selected from the class consisting of C to C polyol esters of C to C fatty acids and polyethenoxy non-ionic oil-in-water emulsifiers, the emollient base having a melting point between about 65 and C.,

(b) sufficient water emulsified with the emollient base to provide a cream-like consistency to the emollient base, said emulsified components (a) and (b) having intimately dispersed therein,

(0) a solid basic material selected from the class consisting of guanadine and alkali and alkaline earth metal hydroxides, carbonates, silicates, and tribasic phosphates in an amount sufiicient to provide a pH in the resulting admixture of 10.5 to 12.5, and

(d) as the essential active depilating agent, about 3 to 15 percent by weight based on the final depilatory amount of a substituted thiol in which the hydrogen atom in hydrogen sulfide is substituted by an organic residue containing two to four carbon atoms and at least one of a group selected from the class consisting of hydroxyl, ketone, aldehyde, ether, amine, sulfonic acid, carboxylic acid and carboxylic acid salt groups.

2. A stable depilatory composition consisting essentially of (a) about 10 to 25 percent by weight based on the final depilatory composition of an emollient base comprising from about 30 to 70 percent by weight of at least one monoamide of a C to C monocarboxylic acid and an alkanolamine selected from the class consisting of lower alkanolamines having primary and secondary amino groups and having only lower alkyl and lower hydroxyalkyl substituents, from about 15 to about 30 percent by weight of at least one Kritchevsky condensate of a C to C monocarboxylic acid and an alkanolamine selected from the class consisting of lower alkanolamines having primary and secondary amino groups and having only lower alkyl and lower hydroxyalkyl substituents, the Kritchevsky condensate having an acid number from about 40 to 60 and an alkali number from about 70 to 200, and from about 15 to 50 percent by weight of a non-ionic oil-in-water emulsifier selected from the class consisting of C to C polyol esters of C to C fatty acids and polyethenoxy non-ionic oil-in-water emulsifiers, the emollient base having a melting point between about 65 and 100 C.,

(b) about 50 to 70 percent by weight based on the final depilatory composition of water emulsified with the emollient base to provide a cream-like consistency to the emollient base, said emulsified components (a) and ([2) having intimately dispersed therein,

(c) about 4 to 15 percent by weight based on the final depilatory composition of a solid basic material selected from the class consisting of guanadine and alkali and alkaline earth metal hydroxides, carbonates, silicates, and tribasic phosphates in an amount 7 8 sufficient to provide a pH in the resultingadmixture emollient base to provide a cream-like consistency of 10.5 to 12.5, and V to the emollient base, said emulsified components (d) as the essetnial active depilating agent, about 3 to (a) and (b) having intimately dispersed therein,

15 percent by weight based on the final depilatory (c) about 4 to 15 percent by weight based on the final composition of -a material selected from the class con- 5 depilatory composition of calcium hydroxide to prosisting of guanadine, ethylene diamine, alkali metal vide a pH in the resulting admixture of 10.5 to 12.5, and alkaline earth metal salts of thioglycollic acid and V and thiolactic acid. (d) as the essential active depilating agent, about 3 to 3. A stable depilatory composition consisting essentialpercent by Weight based on the final depilatory ly of 10 composition of calcium thioglycollate.

(a) about 10 to percent by weight based on the final depilatory composition of an emollient base consist- References Cited in the file Of this Patent ing of from about to 70 percent by weight of at UNITED STATES PATENTS least one monoamide of a C to C monocarboxylic acid and monoethanolamine, from about 15 to about 15 2089212 Kritchevsky 1937 30 percent by weight of at least one Kritchevsky OTHER REFERENCES condensate of a C6 to C22 monocarboxylic acid and Goldsmith: Chemical Reviews, vol. 33 No. 3, pages diethanolamine, the Kritchevsky condensate having 326432, December 1943 an acld number from about to and an alkah Kroll et al.: Drug and Cosmetic Industry, vol. 79, No. number from about 70 to 200, and from about 15 to 20 2, pages 186, 187 272477 August 1956 50 196mmt by weight of Sorbitan trioleate: the emol Dutton et al.: Manufacturing Chemist, vol. 28, N0. 4, lient base having a melting point between about Pages 17 4 0 April 1957 and Sagarin: Cosmetics: Science and Technology, published about 50 to Percent y Weight based on the final by Interscience Publishers, Inc., New York, 1957, pages depilatory composition of water emulsified with the 25 466-470.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No, 3, 154,470 October 27,, 1964 Ernest Braun et a1 It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Column 6, line 36 for "amount" read composition column 7,' line 3, for

"essetnial" read essential Signed and sealed this 6th day of April 1965,

SEAL) Attest:

ERNEST W. SWIDER' EDWARD J. BRENNER Attesting Officer Commissioner of Patents 

1. A STABLE DEPILATORY COMPOSITION CONSISTING ESSENTIALLY OF (A) AN EMOLLIENT BASE COMPRISING FROM ABOUT 30 TO 70 PERCENT BY WEIGHT OF AT LEAST ONE MONOAMIDE OF A C6 TO C22 MONOCARBOXYLIC ACID AND AN ALKANOLAMINE SELECTED FROM THE CLASS CONSISTING OF LOWER ALKANOLAMINES HAVING PRIMARY AND SECONDARY AMINO GROUPS AND HAVING ONLY LOWER ALKYL AND LOWER HYDROXYALKYL SUBSTITUENTS, FROM ABOUT 15 TO ABOUT 30 PERCENT BY WEIGHT OF AT LEASE ONE KRITCHEVSKY CONDENSATE OF C6 TO C22 MONOCARBOXYLIC ACID AND AN ALKANOLAMINE SELECTED FROM THE CLASS CONSISTING OF LOWER ALKANOLAMINES HAVING PRIMARY AND SECONDARY AMINO GROUPS AND HAVING ONLY LOWER ALKYL AND LOWER HYFROXYALKYL SUBSTITUENTS, THE KRIRCHEVSKY CONDENSATE HAVING AN ACID NUMBER FROM 40 TO 60 AND AN ALKALI NUMBER FROM ABOUT 70 TO 200, AND FROM ABOUT 15 TO 50 PERCENT BY WEIGHT OF A NONIONIC OIL-IN-WATER EMULSFIER SELECTED FROM THE CLASS CONSISTING OF C3 TO C15 POLYOL ESTERS OF C6 TO C22 FATTY ACIDS AND POLYETHENOXY NON-IONIC OIL-IN-WATER EMULFSIFIERS, THE EMMOLIENT BASE HAVING A MELTING POINT BETWEEM 65* AND 100* C., (B) SYFFICIENT WATER EMULSIFIED WITH THE EMOLLIENT BASE TO PROVIDE A CREAM-LIKE CONSISTENCY TO THE EMOLLIENT BASE, SAID EMULSFIED COMPONENTS (A) AND (B) HAVING INTIMATELY DISPERSED THEREIN, (C) A SOLID BASIC MATERIAL SELECTED FROM THE CLASS CONSISTING OF GUANADINE AND ALKALI AND ALKALINE EARTH METAL HYDROXIDES, CARBONATES, SILICATES, AND TRIBASIC PHOSPHATES IN AN AMOUNT SUFFICIENT TO PROVIDE A PH IN THE RESULTING ADMIXTURE OF 10.5 TO 12.5, AND (D) AS THE ESSENTIAL ACTIVE DEPILATING AGENT, ABOUT 3 TO 15 PERCENT BY WEIGHT BASED ON THE FINAL DEPILATORY AMOUNT OF SUBSTITUTED THIOL IN WHICH THE HYDROGEN ATOM IN HYDROGEN SULFIDE IS SUBSTITUTED BY AN ORGANIC RESIDUE CONTAINING TWO TO FOUR CABRON ATOMS AND AT LEAST ONE OF A GROUP SELECTED FROM THE CLASS CONSISTIND OF HYDROXYL, KETONE, ALDEHYDE, ETHER, AMINE, SULFONIC ACID, CARBOXYLIC ACID AND CARBOXYLIC ACID SALT GROUPS. 